Patent GB-648842-A (GB)
Title: Improvements in or relating to methods of preserving rubber and the vulcanized rubber product resulting therefrom
IPC: C08K5/3437
Filed: 1947-07-31
Abstract: A copolymer of butadiene and styrene or of butadiene and acrylonitrile is preserved by treating with the condensation product of an aliphatic or cycloaliphatic ketone and a primary amine having the general formula <FORM:0648842/IV (a)/1> in which each R is an ortho arylene group, preferably a phenylene group, at least one of which bears a primary amino group, and X is a non-metallic divalent bridge-forming group completing a five-membered ring, said bridging group comprising an element which forms a heat-stable hydride, any valencies in excess of two being satisfied by hydrogen.  Preferably X is a methylene group, or an oxygen or sulphur atom, and one only of the arylene groups bears a primary amino group.  The ketone is preferably acetone, preferred amines being 2-aminofluorene, 2-aminodibenzofuran and 3-aminodibenzopyrrole.  The Specification contains lists of other suitable ketones and amines (see Group IV (b)).  The Specification as open to inspection under Sect. 91 refers also to the use of aromatic ketones such as acetophenone, benzophenone and benzoyl acetone.  This subject-matter does not appear in the Specification as accepted.ALSO:The Specification relates to the preparation of the condensation product of an aliphatic or cycloaliphatic ketone and a primary amine having the general formula <FORM:0648842/IV (b)/1> in which each R is an ortho arylene group at least one of which bears a primary amino group and X is a non-metallic bridge-forming group comprising an element which forms a heat-stable hydride, any valencies in excess of two being satisfied by hydrogen. Preferably X is a methylene group or an oxygen or sulphur atom, and one only of the arylene groups bears a primary amino group. The condensation product, which is stated to be a quinoline derivative, may be prepared by passing the vapour of the ketone into the hot amine, by refluxing or fusing the ketone with the amine, or by heating the mixture under pressure in an autoclave, in the presence of a catalyst which may be iodine, sulphuric acid, benzene sulphonic acid, p-toluene sulphonic acid, or bromine.  The ketone may be acetone, diacetone alcohol, mesityl oxide, phorone, isophorone, methyl ethyl ketone, diethyl ketone, di-n-propyl ketone, di-isopropyl ketone, methylisobutyl ketone, 2 - hydroxy - 4 - pentanone, monochloroacetone, dichloroacetone, acetonyl acetone, ethylidene acetone, allyl acetone, hydroxy acetone, cyclohexanone or methyl cyclohexanone.  The amine may be aminodibenzofuran, amino-a a -dinaphthofuran, amino - b b  - dinaphthofuran, amino - iso - dinaphthofuran, amino-dinaphthothiophen, amino - dibenzothiophen, amino - chrysofluorene, amino - iso - naphthofluorene, amino - picenefluorene, amino - a a  - dinaphthofluorene, amino-b b -dinaphthofluorene, amino-dibenzopyrrole, or one of the amino-naphthobenzopyrroles, the amino-dinaphthopyrroles or the amino-phenanthrobenzopyrroles.  The Specification as open to inspection under Sect. 91 refers also to the use of aromatic ketones such as acetophenone, benzophenone and benzoyl acetone.  This subject-matter does not appear in the Specification as accepted.ALSO:Natural or synthetic rubber is preserved by treating with the condensation product of an aliphatic or cycloaliphatic ketone and a primary amine having the general formula <FORM:0648842/V/1> in which each R is an ortho arylene group, preferably a phenylene group, at least one of which bears a primary amino group, and X is a non-metallic divalent bridge-forming group completing a five-membered ring, said bridging group comprising an element which forms a heat-stable hydride, any valencies in excess of two being satisfied by hydrogen.  Preferably X is a methylene group or an oxygen or sulphur atom, and one only of the arylene groups bears a primary amino group.  The ketone is preferably acetone, preferred amines being 2-amino-fluorene, 2-aminodibenzofuran and 3-amino-dibenzopyrrole.  The Specification contains lists of other suitable ketones and amines (see Group IV (b)).  The Specification as open to inspection under Sect. 91 refers also to the use of aromatic ketones such as acetophenone, benzophenone and benzoyl acetone.  This subject-matter does not appear in the Specification as accepted.